What I Know about Wrestling with Regret and Winning

Last week Jeff and I drove over to the college to exercise. We wanted a change from our usual path around the neighborhood. We're walking and climbing bleachers to prepare for our next hiking adventure. I was shivering under my hoodie and we weren’t talking much because of the wind. It’s April and the azaleas are blooming though they’ve been timid with the cooler than normal weather we’ve been having. We noticed as we walked by the school under construction, the work is nearing completion. The concrete curbs have been poured and the ground is being groomed for paving. 

We are nearing a completion of our own, the project of our lives together. Luke will be married at the end of the week, our third and last child will fly forever. Our parenting duties are ending. I mentioned this plain fact to Jeff as the sun slid out of sight. 

His acknowledgment of our present transition came as a question, “Do you have any regrets?”

“Of course, I do,” I said, “but I’ve been processing them.” He wasn’t surprised. 

Regret is inevitable if we have any memory at all. The key to dealing with regret well is determined by our choice to allow it to be a bully that punches us in the gut with shame day after day, or whether we allow our experience to become part our training toward maturity in our lives and in our faith.

Regret often expresses itself in the words “if only.” When we consider our actions (or inaction) in the past against what we know in the present, we see how outcomes could have been different if we had acted another way. As the old adage goes—hindsight is 20/20. We can give ourselves grace because much of what we regret arises out of what we learned from the experience. We comfort ourselves with the knowledge that most of the time (although not always) we were doing the best that we could. We didn’t know then what we know now.

So what do we do with regret? As I meditated and studied the story of Jacob returning to the land of his father in Genesis 32-33, Jacob’s story and my own inspired these thoughts about the very real dilemmas concerning the common emotion.

Be Courageous

Courage always assumes vulnerability. Jacob became vulnerable when he turned back toward Canaan after 20 years of being away. Going home meant facing his past. When we own our need for healing regarding our past mistakes and failures, we are positioning ourselves to receive that healing. Regret wants to hold us in the past and keep us from our future. For those of us in Christ, our regrettable actions and the regrettable actions of others against us are opportunities for the abounding grace of God in our lives and theirs. 

Making the journey toward a whole heart is a spiritual battle against spiritual forces. We need to recognize the enemy and use the weapons at our disposal to defeat him. The power of repentance, confession, and forgiveness turn the enemy on his heels. Instead of grasping tenaciously to regret, we need to take “the shield of faith in one hand and the sword of the Spirit in the other[1].”

Accept What Is

The present is the only time we really have. Hindsight left unchecked forces us into the despair of what cannot be changed. Our do-overs happen in the present as we make better decisions than we once did. We can choose to let our losses become our gains. Our discernment and wisdom have increased because of the things we have suffered. We express our faith when we can say confidently that God has used all things to shape our lives, even things that we regret. By asking for and receiving forgiveness, we allow God to redeem our past. 

Make Amends

We need to be ready to make amends if we want to have freedom from regret. On his journey back to the land of promise, Jacob sent a peace offering ahead to Esau. He was nervous about meeting him again and anticipated the worst. When they finally met up, Esau refused the gift and embraced his estranged brother. Jacob insisted that he take the gift. Both brothers have something to teach us in this interaction concerning reconciliation. The truth is we can try to make amends, but we cannot control the way another receives our offer. Leaving the outcome to God frees us from further regret.

Wrestle it out

Regret tells us who we were. Blessing tells us who we will be. Living past regret is a wrestling match with ourselves and with God. My greatest regret was the season of mental illness and depression I experienced while my kids were young. They didn’t have the momma they wanted and needed. Now almost 20 years since those days of darkness, I could live with regret. I could let that experience define my life, but by God’s grace I found the courage to face the disappointment and pain of those difficult days and move past them. I wrestled for many years holding on for the blessing. Like Jacob whose name became Israel, I received an inheritance I can give to my children— my healing. I determined to take hold of the blessing of God. My healing is more than coping. It is full and real. Grace.

I’m not special; I’m loved and restored. Jesus offers freedom from regret to anyone who has the courage to face their fear and let him transform it. He offers it to you.

Jeff and I will be crossing the creek this weekend, taking the next steps on our journey. Regret won’t be going in our backpacks. By the grace of God, we still have mountains to climb.

[1] Beth Moore, The Quest Bible Study video

It has occurred to me that in every picture I put on my blog, I'm wearing the hot pink wind jacket. Regrettable. :)


  1. Thank you for this post. Regret is a burden I pick up far too often. Your words will help me resist. And you look GREAT in hot pink ;)


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